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Featured Apartments in Chestertown

Estimated price for 1 night/2 adults

Historic & Quaint Room Downtown Middletown, DE Awaits You!
Historic & Quaint Room Downtown Middletown, DE Awaits You!
Middletown, Delaware
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Situated in Middletown, this apartment building is close to Frog Hollow Golf Club. Area attractions also include Historic Houses of Odessa and Back Creek Golf ...
Historic & Quaint Room Downtown Middletown, DE
Historic & Quaint Room Downtown Middletown, DE
Middletown, Delaware
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Relax on the Eastern Shore of Kent Narrows in a King Bed
Relax on the Eastern Shore of Kent Narrows in a King Bed
Grasonville, Maryland
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5.0/5 (1 reviews)

This might be the most impressed I have been with any rental property, ever! Jackie went above and beyond to ensure that we had everything we need--and I mean EVERYTHING (toothbrushes, toothpaste, sunblock (his and hers), deodorant, shoe care kit, shower caps, shampoo, ponchos, umbrellas, lotion, ...

Reviewed on Jul 25, 2018
Situated in Grasonville, this romantic apartment building is within 3 mi (5 km) of Queenstown Premium Outlets, Queenstown Harbor Golf Links, and Queenstown Harbor ...
Historic & Quaint Room in the Center of Downtown Middletown,de
Historic & Quaint Room in the Center of Downtown Middletown,de
Middletown, Delaware
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Situated in Middletown, this historic apartment building is close to Frog Hollow Golf Club. Area attractions also include Historic Houses of Odessa and Back ...
Global Luxury Suites at Toone Street
Global Luxury Suites at Toone Street
4.0 out of 5.0 3700 Toone Street, Baltimore, MD
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Located in Downtown Baltimore, this apartment building is 0.4 mi (0.7 km) from Canton Waterfront Park and within 3 mi (5 km) of Inner Harbor and Johns Hopkins ...
Stay And Play In Downtown Annapolis
Stay And Play In Downtown Annapolis
Annapolis, Maryland
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4.8/5 (21 reviews)

Perfect location to walk to everything in Annapolis. The apartment was just as described on line. Open space, clean, dishes to use - all in all a great place and price easily matches accommodation.

Reviewed on Jul 7, 2019
Located in the heart of Annapolis, this historic apartment building is within a 5-minute walk of Hammond-Harwood House and William Paca House. Maryland State ...
Discounted Rates, Across From Gate 1 Usna, 1 Block to the Downtown Harbor
Discounted Rates, Across From Gate 1 Usna, 1 Block to the Downtown Harbor
Annapolis, Maryland
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4.9/5 (48 reviews)

Overall, everything about our stay was perfect! The location, the set-up, the owners... Everything .. They couldn't have been nicer or more helpful. Everything was very clean and worked! My mid was thrilled to bring and do some laundry while we were visiting. Just worked out PERFECTLY. We will definitely ...

Reviewed on Feb 6, 2019
Located in Historic District, this historic apartment building is within a 5-minute walk of Annapolis City Dock and William Paca House. Maryland State House ...
Amazing River House Waterfront Apartment on Choptank River on 18 Acre Farm
Amazing River House Waterfront Apartment on Choptank River on 18 Acre Farm
Greensboro, Maryland
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4.8/5 (25 reviews)

Helen and Peter take pride in their rental! They make sure that everything is perfect for their guests! The extra touches such as the homemade cookies upon arrival to the breakfast foods waiting for you in the refrigerator make your stay perfect! Their rental provides you with the perfect setting ...

Reviewed on Sep 23, 2018
Located in a rural location, this family-friendly apartment building is 5.9 mi (9.5 km) from Martinak State Park and 11.9 mi (19.1 km) from Adkins Arboretum. ...
Global Luxury Suites at Brewers Hill
Global Luxury Suites at Brewers Hill
4.0 out of 5.0 1200 Conkling Street, Baltimore, MD
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4.0/5 (1 reviews)

great stay - difficult to check in

Reviewed on Feb 26, 2017
Located in Canton, this apartment building is 0.4 mi (0.6 km) from Canton Waterfront Park and within 3 mi (5 km) of Johns Hopkins Hospital and National Aquarium ...
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Estimated price for 1 night/2 adults

Holiday Inn Express Hotel & Suites Chestertown

Holiday Inn Express Hotel & Suites Chestertown

150 Scheeler Road, Chestertown, MD
    2.5 out of 5.0
     
     
    4.3 out of 5 (319 reviews)

    Holiday Inn Express Hotel & Suites Chestertown$87

    Jul 21 - Jul 22

    Holiday Inn Express Hotel & Suites Chestertown$87
    Driftwood Inn

    Driftwood Inn

    609 Washington Avenue, Chestertown, MD
      2.0 out of 5.0
       
       
      2.1 out of 5 (99 reviews)

      Driftwood Inn$69

      Jul 17 - Jul 18

      Driftwood Inn$69

      Staying in an Apartment in Chestertown


      There are 9 lodging options in Chestertown. Though there aren't many apartments, we can help you find accommodations that are similar. When you search on Expedia, you can use the filters to search for a kitchen— just one of the conveniences you might find in an apartment. You can also filter by similar property types like vacation homes, condos, or cabins.


      Here are some of the top apartments in the area:

      Stay And Play In Downtown Annapolis:

      • Located in Annapolis , 26.2 mi/42.1 km from the city center
      • Includes a patio, a living room, and a fireplace

      Global Luxury Suites at Toone Street:

      • Free WiFi, a washer/dryer, and a living room included
      • Located 25.7 mi/41.4 km away in Baltimore
      • An outdoor pool and a 24-hour fitness center on site

      Global Luxury Suites at Brewers Hill:

      • It's located in Baltimore, 25.8 mi/41.6 km away
      • Includes free WiFi, a washer/dryer, and a living room
      • A 24-hour fitness center and a 24-hour business center on site

      Relax on the Eastern Shore of Kent Narrows in a King Bed:

      • A fireplace included
      • Located 17.6 mi/28.4 km away in Grasonville

      Waterfront Apartment Kent Island. Close to Wedding Venues:

      • Located in Stevensville , 23.6 mi/38 km from Chestertown
      • Includes a patio and a living room
      • A fitness center and a spa tub on site


      When is the Best Time to Visit Chestertown?


      Though weather is just one factor, it can really affect your travel plans, especially if you are planning a longer stay. Since apartments often have more stringent cancellation policies, it’s good to familiarize yourself with these seasonal weather averages before booking.


      • The hottest months are typically July and August, while January and February are the coldest months
      • January-March: Daytime temperatures average 58° F and nighttime temperatures average 25° F
      • April-June: 85° F is the daytime average and 39° F is the nighttime average
      • July-September: Daytime averages are around 87° F and nighttime averages are around 53° F
      • October-December: The average temperatures are 73° F during the day and 28° F at night
      • Average rainfall is 1.42 inches in a year

      Things to Do in Chestertown


      Cultural attractions include Garfield Center for the Arts at the Prince Theater and Historical Society of Kent County Maryland, whereas Wilmer Park is one spot to enjoy nature. Washington College and Rolphs Wharf Marina are a couple of places you'll find in the larger area.


      Chestertown is known also for its:
      • Sports
      • University life
      • Festivals
      • Boating
      • Historical sites
      • Art
      • Wildlife

      How to Get to Chestertown and Around the Area


      Fly into Baltimore, MD (MTN-Martin State), which is located 19.5 mi (31.4 km) away. Otherwise, look for flights into Easton, MD (ESN-Easton - Newnam), which is 27.3 mi (43.9 km) away. If you'd like to explore around the area, you may want to rent a car for your trip.